Synthesis of cis-vinyltrimethylstannanes and cis-vinylpinacolboronates in a two-step highly regio and stereoselective process

Paul Malek Mirzayans; Rebecca H. Pouwer; Craig M. Williams; Paul V. Bernhardt

doi:10.1016/j.tet.2009.06.092

Synthesis of cis-vinyltrimethylstannanes and cis-vinylpinacolboronates in a two-step highly regio and stereoselective process

Paul Malek Mirzayans, Rebecca H. Pouwer, Craig M. Williams^*, Paul V. Bernhardt

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

A highly efficient two-step regio and stereoselective method for the synthesis of both cis-vinyltrimethylstannanes and cis-vinylpinacolboronates is described. This method takes advantage of the known lithium/tellurium exchange pathway providing a versatile alternative to known literature methods. The methodology presented demonstrates compatibility, for example, with substrates bearing oxygen functionality in comparison to previously reported methods of cis-selective hydrostannylation (i.e., ZrCl₄).

Original language	English
Pages (from-to)	8297-8305
Number of pages	9
Journal	Tetrahedron
Volume	65
Issue number	39
DOIs	https://doi.org/10.1016/j.tet.2009.06.092
Publication status	Published - 26 Sept 2009
Externally published	Yes

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abstract = "A highly efficient two-step regio and stereoselective method for the synthesis of both cis-vinyltrimethylstannanes and cis-vinylpinacolboronates is described. This method takes advantage of the known lithium/tellurium exchange pathway providing a versatile alternative to known literature methods. The methodology presented demonstrates compatibility, for example, with substrates bearing oxygen functionality in comparison to previously reported methods of cis-selective hydrostannylation (i.e., ZrCl4).",

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AU - Pouwer, Rebecca H.

AU - Williams, Craig M.

AU - Bernhardt, Paul V.

PY - 2009/9/26

Y1 - 2009/9/26

N2 - A highly efficient two-step regio and stereoselective method for the synthesis of both cis-vinyltrimethylstannanes and cis-vinylpinacolboronates is described. This method takes advantage of the known lithium/tellurium exchange pathway providing a versatile alternative to known literature methods. The methodology presented demonstrates compatibility, for example, with substrates bearing oxygen functionality in comparison to previously reported methods of cis-selective hydrostannylation (i.e., ZrCl4).

AB - A highly efficient two-step regio and stereoselective method for the synthesis of both cis-vinyltrimethylstannanes and cis-vinylpinacolboronates is described. This method takes advantage of the known lithium/tellurium exchange pathway providing a versatile alternative to known literature methods. The methodology presented demonstrates compatibility, for example, with substrates bearing oxygen functionality in comparison to previously reported methods of cis-selective hydrostannylation (i.e., ZrCl4).

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U2 - 10.1016/j.tet.2009.06.092

DO - 10.1016/j.tet.2009.06.092

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ER -

Synthesis of cis-vinyltrimethylstannanes and cis-vinylpinacolboronates in a two-step highly regio and stereoselective process

Abstract

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